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Chapter 30: Q25 E (page 1033)

Which of the following reactions is more likely to occur? Explain.

Short Answer

Expert verified

To identify which among the two reactions is more likely to occur can be stated.

Step by step solution

01

Statement for the first reaction

The involvement of reaction 1 has reverse (4+2) cycloaddition. There is an involvement for three electron pairs. There is an involvement of molecular orbitals arranged in such a way that the reaction will states with suprafacial geometry under thermal conditions.

02

Statement for the second reaction

The involvement of reaction 2 has a reverse (2+2) cycloaddition reaction. There is an even electron pair number involved. The thermal reaction will require an antarafacial geometry. There is no possibility in the arrangement for reactant molecular orbitals. This reverse addition reaction will have no possibility to occur.

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Most popular questions from this chapter

The 13C NMR spectrum of homotropilidene taken at room temperature shows only three peaks. Explain.

Karahanaenone, a terpenoid isolated from oil of hops, has been synthesized by the thermal reaction shown. Identify the kind of pericyclic reaction, and explain how karahanaenone is formed.

What stereochemistry—antarafacial or suprafacial—would you expect to observe in the following reactions?

(a) A photochemical [1,5] sigmatropic rearrangement

(b) A thermal [4 + 6] cycloaddition

(c) A thermal [1,7] sigmatropic rearrangement

(d) A photochemical [2 + 6] cycloaddition

Photolysis of the cis-cyclobutene isomer in Problem 30-35 yields cis-cyclododecaen-7-yne, but photolysis of the trans isomer yields trans-cyclododecaen-7-yne. Explain these results, and identify the type and stereochemistry of the pericyclic reaction.

Answer Problem 30-22 for the thermal and photochemical cyclizations of (2E,4Z,6Z,8Z)-2,4,6,8-decatetraene.
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